Diisopropylethylamine → HCID 68590970, compound

HRID 1429161Notes

Reaction equation

HRID 1429161 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:18][CH:17]([O:19][C:20]3[CH:25]=[C:24]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[N:23]=[C:22]([O:32][CH3:33])[N:21]=3)[CH2:16][CH:15]2[C:34]([OH:36])=O)=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2].Cl.[CH3:38][NH:39][CH:40]=[CH:41][CH2:42][CH2:43][CH2:44][CH3:45].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(=O)([O-])O.[Na+]>>[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:18][CH:17]([O:19][C:20]3[CH:25]=[C:24]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:23]=[C:22]([O:32][CH3:33])[N:21]=3)[CH2:16][CH:15]2[C:34](=[O:36])[N:39]([CH2:40][CH2:41][CH2:42][CH2:43][CH:44]=[CH2:45])[CH3:38])=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2]

Participants

6

Reactant 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68592750HCID 68592750, compoundHCID 86641379HCID 86641379, compound

Product 1

HCID 68590970HCID 68590970, compound

Procedure

To a ice cooled solution of the crude acid 13b (1.2 g, 1.81 mmol), N-methylhexeneamine hydrochloride (0.404 g, 2.7 mmol) and DIEA (1.2 g, 9.1 mmol) was added HATU (1.02 g, 2.7 mmol) and the mixture was stirred for twenty minutes on an ice bath and two hours at room temperature. A saturated solution of sodium hydrogen carbonate was added and the mixture was extracted three times with ethyl acetate. The combined organic phases were washed with saturated sodium hydrogen carbonate and brine and dried with sodium sulphate, filtered and evaporated under reduced pressure. The product was isolated by silica gel chromatography with hexane ethyl acetate, (0.8 g, 74%), (M+H)+591.

Workup

  1. extractionthe mixture was extracted three times with ethyl acetate
  2. washThe combined organic phases were washed with saturated sodium hydrogen carbonate and brine
  3. dry with materialdried with sodium sulphate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe product was isolated by silica gel chromatography with hexane ethyl acetate, (0.8 g, 74%), (M+H)+591

Sources & evidence

ORD record
ord-eb78dca7df8a4de4ae277cb7367fe51c
Source dataset
uspto-grants-2015_01
Patent number
US08937080B2

Reaction notes

Loading…